ENZYMATIC RESOLUTION OF THE ETHYL ACETALS OF (R)-4-HYDROXYALK-2-YNALS AND (S)-4-HYDROXYALK-2-YNALS

被引：11

作者：

ALLEVI, P ^{[1
]}

ANASTASIA, M ^{[1
]}

CAJONE, F ^{[1
]}

CIUFFREDA, P ^{[1
]}

SANVITO, AM ^{[1
]}

机构：

[1] UNIV MILAN,CNR,CTR PATOL CELLULARE,IST PATOL GEN,I-20133 MILAN,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 01期

关键词：

D O I：

10.1016/S0957-4166(00)80472-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

4-hydroxyalk-2-ynals diethylacetals have been efficiently resolved by enatioselective acetylation mediated by Pseudomonas fluorescens lipase affording the acetylated (R)-enantiomers in preference, independent of the length and bulk of the alkyl substituent at the carbinol group. Reduction with LiAlH4 of unreacted or acetylated isomers affords the corresponding ethylenic acetals with the hydrogen deriving from the hydride in the beta position in respect to the allylic hydroxyl.

引用

页码：13 / 16

页数：4

共 20 条

[1] ALLEVI P, 1993, JUN SFRR SUMM M SIEN
[2] ALLEVI P, 1993, J ORG CHEM, V58, P5002
[3] ALLEVI P, 1992, FREE RADICAL RES COM
[4] IDENTIFICATION OF 4-HYDROXYNONEAL AS A CYTO-TOXIC PRODUCT ORIGINATING FROM THE PEROXIDATION OF LIVER MICROSOMAL LIPIDS
BENEDETTI, A
COMPORTI, M
ESTERBAUER, H
[J]. BIOCHIMICA ET BIOPHYSICA ACTA, 1980, 620 (02) : 281 - 296
[5] 4-HYDROXYNONENAL INDUCES A DNA-BINDING PROTEIN SIMILAR TO THE HEAT-SHOCK FACTOR
CAJONE, F
SALINA, M
BENELLIZAZZERA, A
[J]. BIOCHEMICAL JOURNAL, 1989, 262 (03) : 977 - 979
[6] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS
CHEN, CS
FUJIMOTO, Y
GIRDAUKAS, G
SIH, CJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) : 7294 - 7299
[7] COPPOLA GM, 1984, SYNTHESIS-STUTTGART, P1021
[8] A NEW STEREOSPECIFIC SYNTHESIS OF TRISUBSTITUTED OLEFINS . STEREOSPECIFIC SYNTHESIS OF FARNESOL
COREY, EJ
KATZENEL.JA
POSNER, GH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (16) : 4245 - &
[9] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES
DALE, JA
DULL, DL
MOSHER, HS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) : 2543 - &
[10] SYNTHESIS OF A NOVEL PROSTAGLANDIN H-2 (PGH2) ANALOG
ELDER, JS
MANN, J
WALSH, EB
[J]. TETRAHEDRON, 1985, 41 (15) : 3117 - 3125

← 1 2 →